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20 The Everly Brothers: "So Sad (To Watch Good Love Go Bad)," from It's Everly Time (Warner Brothers, 1960) A descending scale begins a classic of sad restraint: "We used to have good times together but now I feel them slip away/It makes me cry to see love die: so sad to watch good love go bad..." Sparse backing and note-perfect harmony compliment one of Don’s greatest lyrics. The inspiration for many a tender hearted ne’r-do-well, from John Lennon to Brian Wilson and beyond.

19 The Band: "It Makes No Difference," from Northern Lights - Southern Cross (Capitol, 1975) The most artless--and most piningly desolate--love song Robbie Robertson ever wrote, sung with hopeless tenderness by Rick Danko, The Band's most artless singer. "I love you so much, and it's all I can do/Just to keep myself from telling you/That I never felt so alone before..."

18 Randy Crawford: "One Day I'll Fly Away," single (Warner Brothers, 1980) "When will love be through with me?" MOR slush to some ears, this Crusaders/Will Jennings-constructed jazz-funk-lite ballad remains irresistibly sad to many others--especially when Crawford trails off on "away" and the swelling chord drops down beneath her. Tremulous and dreamily lovely.

17 Soft Cell: "Say Hello, Wave Goodbye," single (Some Bizzare, 1982) The genius of this synthpop classic is the way it starts out as a bitchfest--Marc Almond coming on like Dusty Springfield's petulant little sister--and then suddenly flips into a deep, engulfing sadness. Even as Almond demands that his lover take her hands off him and claims that "You never knew me/I never knew you", Dave Ball's oceanic keyboard chords say the opposite--that Marc is all tetchy bravado and that this parting is bursting his heart.

16 Billie Holiday: "Don't Worry 'Bout Me," from Lady In Autumn (Verve, 1959) Billie is being so damn reasonable: "Why not call it a day the sensible way, and still be friends," she sings. And do we believe her? We do not. Her apparent acceptance that "our little show is over" cuts no ice when delivered with such cracked desperation. Truly heart-rending late Lady Day.

15 Love: "Alone Again Or," from Forever Changes (Elektra, 1967) Love’s most famous recording: written, ironically, not by leader Arthur Lee but by po' little rich boy Bryan Maclean. "I heard a funny thing, somebody said to me/‘You know that I could be in love with almost everyone/I think people are the greatest fun’. And I will be alone again tonight, my dear..." The bastard son of the Byrds meets Ennio Morricone--all West Coast harmonies, 12-string guitars and Tijuana brass--this ode to loneliness seemed to come out of nowhere in late ‘67.

14 The Pretenders: "I Go To Sleep," from Pretenders II (WEA, 1981) What a concept: a song about missing an ex-partner sung by your future ex-partner. Written by Ray Davies and sung by Chrissie Hynde, this gives a peek into the--one assumes--charred lansdscape of the Davies/Hynde relationship. A perfect marriage of arrangement (including a beautiful French horn riff), lovelorn vocals and passionate lyrics: "I was wrong, I will cry, I will love you ‘til the day I die/You alone, you alone and no-one else/You were meant for me..."

13 Dusty Springfield: "I Just Don't Know What To Do With Myself," single (Phonogram, 1964) Springfield here performs a rare feat: outperforming Dionne Warwick's own version of a Bacharach and David classic. Moving from forlorn whimper to gutsy roar, she lives the song to the full. "Going to the movies only makes me sad; parties make me feel as bad/When I'm not with you, I just don't know what to do." Decimating.

12 Little Feat: "Long Distance Love," from The Last Record Album (Warner Brothers, 1975) "Does she know she hurt me so?" How did a sad ballad get so funky and stay so sad? Lowell George was never more soulfully vulnerable than on this late-flowering gem from an otherwise indifferent Feat platter.

11 Smokey Robinson & the Miracles: "The Tracks Of My Tears," from Going To A Go-Go (Motown, 1965) Bob Dylan called Smokey "America’s greatest living poet" with good reason. The guy was able to take the most everyday images and imbue them with a real emotional strength, allowing even the flyest guy to wear his heart on his sleeve: "People say I’m the life of the party ‘cos I tell a joke or two/My smile is the make-up I wear since my break up with you..." Couple that with Marv Tarplin's peerless, aching melody and you've got the ultimate Motown heartbreaker.

10 Bonnie Raitt: "I Can't Make You Love Me," from The Luck Of The Draw (Capitol, 1991) "I'll feel the power, but you won't..." It's all very "tasty" and L.A.-musoid, this smokey ballad of resignation to loss, but it also rings hauntingly true as an articulation of honesty in the midst of misery--which makes it as much a song of healing as anything else.
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http://new.music.yahoo.com/blogs/rocksbackpages/520/cry-me-a-river-the-20-most-heartbreaking-songs-of-all-time/

Bubba Dawg

11-30-2008, 10:12 AM

Great post megimoo.

A couple of these i never heard, but some real tear jerkers.

I might add Last Kiss by Pearl Jam (and others).

Well where O where can my Baby be
The Lord took her away from me.
She's gone to Heaven so I've got to be good
So I can see my Baby when I leave this world.

OwlMBA

11-30-2008, 10:06 PM

Was this list written by someone who is 60 years old? There are a lot, lot better "heartbreak" songs that didnt make this list.

Bubba Dawg

11-30-2008, 10:21 PM

Was this list written by someone who is 60 years old? There are a lot, lot better "heartbreak" songs that didnt make this list.

Good question. The thing with these lists is that they are, in general, limited by the musical tastes of the ones making the list.

Lots of more recent heartbreak songs could be named.

What's on the list could be added to. I'd like to see that.

Bubba Dawg

11-30-2008, 10:28 PM

Tears in Heaven, by Clapton, comes to mind....

Celtic Rose

11-30-2008, 11:25 PM

Tears in Heaven, by Clapton, comes to mind....

Such a sad song. :(

Bubba Dawg

11-30-2008, 11:28 PM

Such a sad song. :(

It is. I think he wrote it after the death of his child.

I can only imagine such heartbreak.

Celtic Rose

11-30-2008, 11:33 PM

It is. I think he wrote it after the death of his child.

I can only imagine such heartbreak.

Yeah, I think that his little boy strangled in the cord on a set of window blinds. :( Such a sad story, and it just makes the song that much sadder. :(

wilbur

11-30-2008, 11:46 PM

Most heartbreaking song???

A lap-dance is so much better when the stripper is cryin' -Bloodhound Gang

;)

Celtic Rose

11-30-2008, 11:47 PM

Most heartbreaking song???

A lap-dance is so much better when the stripper is cryin' -Bloodhound Gang